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  1. Ad

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    Star Rating
    4 out of 5
    Simpson Bay
    Big Winter Sale
    Book now and enjoy the lovely Caribbean Sea at the best hotel on the Island. Enjoy pools, restaurants free WiFi and more.
    Lower price available
    Price is $190
    per night
    $380 for 2 nights
    4.2/5Very Good(1,101 reviews)
    Click for more information about The Villas at Simpson Bay Beach Resort and Marina
  2. Ad

    Photo gallery

    Star Rating
    4 out of 5
    Pelican Key
    Winter Super Sale
    Enjoy a family beachfront resort where you'll find relaxing sandy beaches. Enjoy Free WiFi, pools, restaurants, and more.
    Lower price available
    Price is $165
    per night
    $331 for 2 nights
    4.0/5Very Good(1,681 reviews)
    Click for more information about Simpson Bay Beach Resort and Marina

  3. Photo gallery

    Star Rating
    4 out of 5
    Pelican Key
    Lower price available
    Price is $165
    per night
    $331 for 2 nights
    4.0/5Very Good(1,681 reviews)
    Click for more information about Simpson Bay Beach Resort and Marina
  4. Say hello to lower prices – just like that!
    Instantly get an extra 10% or more off thousands of properties with Insider Pricing.
    Sign up, it's freeSign in
  5. VIP Access
    Star Rating
    4 out of 5
    Oyster Pond
    Lower price available
    Price is $183
    per night
    $366 for 2 nights
    4.0/5Very Good(414 reviews)
    Reserve now, pay later
    Click for more information about Oyster Bay Beach Resort
  6. Star Rating
    4 out of 5
    Maho Reef
    Lower price available
    Price is $198
    per night
    $397 for 2 nights
    3.6/5Good(415 reviews)
    All meals included
    Click for more information about Sonesta Maho Beach All Inclusive Resort Casino & Spa
  7. Star Rating
    4 out of 5
    Simpson Bay
    Lower price available
    Price is $190
    per night
    $380 for 2 nights
    4.2/5Very Good(1,101 reviews)
    Click for more information about The Villas at Simpson Bay Beach Resort and Marina
  8. Star Rating
    4 out of 5
    Orient Bay
    We have 7 left at 22% off at
    Price was $291Price is now $227
    per night
    $455 for 2 nights
    4.1/5Very Good(352 reviews)
    Breakfast Included
    Click for more information about Esmeralda Resort
  9. Star Rating
    4 out of 5
    Upper Prince's Quarter
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Alizee by RedAwning
  10. Star Rating
    4 out of 5
    Cay Bay Hill
    We are sold out
    Dec 8 - Dec 10
    Click for more information about El Sueno by RedAwning
  11. Star Rating
    4 out of 5
    Orient Bay
    We are sold out
    5.0/5Exceptional(3 reviews)
    Dec 8 - Dec 10
    Click for more information about Villa La Voile Blanche
  12. Star Rating
    4 out of 5
    Cupecoy
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Villa Luna
  14. Star Rating
    4 out of 5
    Orient Bay
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Villa Mapai
  15. Star Rating
    4 out of 5
    Orient Bay
    Unavailable
    Dec 8 - Dec 10
    This property requires you to stay at least 4 nights. Try adding more nights.
    Click for more information about Mango
  16. Star Rating
    4 out of 5
    Lowlands
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Villa Adelaides Escape
  17. Star Rating
    4 out of 5
    Cul de Sac
    Unavailable
    Dec 8 - Dec 10
    This property requires you to stay at least 5 nights. Try adding more nights.
    Click for more information about Casa Branca
  18. Star Rating
    4 out of 5
    Les Terres Basses
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Villa Belle Fontaine
  19. Star Rating
    4 out of 5
    Oyster Pond
    We are sold out
    4.0/5Very Good(596 reviews)
    Dec 8 - Dec 10
    Click for more information about The Westin Dawn Beach Resort & Spa, St. Maarten
  20. Star Rating
    4 out of 5
    Les Terres Basses
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Villa Belle Fontaine
  21. Star Rating
    4 out of 5
    Cupecoy
    We are sold out
    Dec 8 - Dec 10
    Click for more information about Porto Blue
  22. Star Rating
    4 out of 5
    Orient Bay
    Unavailable
    Dec 8 - Dec 10
    This property requires you to stay at least 4 nights. Try adding more nights.
    Click for more information about Villa Hamoa